Category Archives: Chicago Insider Tips

Chicago Insider Tips: What You Need to Know This Week – July 1, 2014

At The Chicago Lifestyle we’re focused on keeping you in the know on what’s hot and happening in Chicago. This week we’re bringing you four tips to add to your list!


go cycle, turf and surf triathlon, standup paddle boarding


Try the New Wave of Triathlons – Spinning, Running and Stand-up Paddle Boarding


Always wanted to join a triathlon but scared of swimming in Lake Michigan? Don’t own a bike? None of that matters when you sign up for Go Cycle’s Turf & Surf Triathlon, held on Sunday, August 3. The race consists of:

  • 12.5 mile indoor cycling at Go Cycle Studio (525 W. North Ave.)
  • 5K run from Oz Park to North Avenue Beach
  • 0.75 mile stand-up paddle on Lake Michigan at North Avenue Beach


Sign up by this Thursday, July 3 for $70, then the price increases to $75.



gilt city, chicago distilling company, distillery tour, whiskey tasting


Impress 5 of Your Friends at a Chicago Distillery Tour and Tasting


Located amidst the popular restaurants on Milwaukee Avenue in Logan Square, Chicago Distilling Company features small batch, locally sourced liquors. Treat 5 or 10 of your friends to a private distillery tour and tasting, thanks to Gilt City’s deal (buy before the deal closes on July 9). Enjoy vodka, gin and white whiskey cocktail samples while learning about the nuances of each type of liquor.



chicago river, edm chicago, chicago music festival


Experience an EDM Concert Over the Chicago River


The Riverwest Music Festival hits Chicago for the first time this weekend – July 4-6 – echoing electronic tunes over a mile-long span on the North Branch of the Chicago River at Elston and Division. Featuring over 40 artists, the concert brings together a great lineup in a unique Chicago setting. Single-day passes are still available here.



chicago race, chicago 10k, grant park race


Run through Grant Park in the Chicago 10K on August 10


Whether you’ve been running all season or you’re just starting to prepare for “bathing suit season,” there’s still time to sign up for the Chicago 10K on Sunday, August 10. The race starts and finishes in Grant Park, and finishing will earn you a pretty sweet medal. Sign up now for $55 before capacity is reached.



Chicago Trolley Adventures: The Good, The Bad, and The Ugly

Chicago Trolley Adventures: The Good, The Bad, and The Ugly


For a crazy, unforgettable night, everyone needs to take part in Chicago’s favorite pastime at least once – a party trolley. Chauffeured around the city in a rented trolley car, you can experience 3 hours of moving dance party sing-a-longs with 24 – 30 of your closest friends. A typical Chicago trolley itinerary involves pick-up at a house or location of your choice, a few stops along the way for bars or photo opportunities, and a drop-off at a final destination – usually a bar or a house.


While this trip might seem like a good chance to get in your Chicago sightseeing, the level of rowdiness of the crowd will make that determination. With all of your friends in tow, you can capture great photos outside the planetarium with the skyline in the background. Additionally, you can visit some of the bars outside your usual boundaries without having to worry about taking multiple cabs. Set up your favorite tunes, stock up on your favorite drinks, and gather your crew for a night around town.


Of course with all privilege comes responsibility – planning a trolley can be a logistical challenge. As with any event, not all parts will go as planned. Here are some tips for navigating what could be the night of your life.


Questions to ask the trolley company:

  • Will your “advanced sound system” amplify my iPod/iPhone playlist?
  • Can we bring our own beverages on board (the answer is usually yes – but no glass)
  • Is the trolley heated/air conditioned, and can the windows be opened?
  • Is gratuity included in the credit card charge, or will the driver expect cash at the end of the ride?
  • Can I get a discounted fare if I “like” you on Facebook?


Questions to ask the bars you want to stop at:

  • Can you accommodate 25 people sometime between 8 – 10 p.m. with no cover and a limited line?


And finally, questions to ask yourself:

  • Am I willing to corral 24 – 30 of my friends and hunt them down for their share of the cost?
  • Do I have the patience for last-minute cancellations and added guests?
  • Do I want to buy all the beverages in advance, or ask guests to BYOB?
  • Am I willing to make sure the trolley is spotless at the end to avoid a cleaning fee?


Other helpful tips:

  • To collect funds in advance, use a service such as Crowdtilt, which allows credit card payments and will divide the total cost among the final number of guests that attend
  • If you bring on beverages, don’t rely on Styrofoam coolers – they will break. Purchase some cheap plastic tubs at WalMart to house your drinks and ice
  • Your playlist sets the mood – but bring good old mix-tape CDs as backup in case they can’t plug in your iPod/iPhone. My approach is to start off with mood-boosting Top 40s, continue with solid dance music, and transition into 80s ballads or 90s rap by the time you’re on your way to the third bar. Consider you’ll need about 2.5 hours of music ready if you’ll be spending one of the three hours on bar stops
  • Bring on trash bags, paper towels, Solo cups, etc. – clean up everything along the way
  • The homeless people outside are always looking for a free beer handout. Proceed with your own discretion
  • Clear communication with the driver is key. Provide an itinerary with addresses in advance, and make sure he/she knows the timing of each bar stop. Tell your guests when to return to the trolley, so no one gets left behind!



Have fun!!!


{Image via Coleman Forredondo}


Your Guide to Living The Chicago Lifestyle: Summer 2014

Your Guide to Living The Chicago Lifestyle: Summer 2014


Our blessed Chicago summer has finally arrived and we all have one goal: Make the most of it! Don your sunglasses and head out the door to enjoy Chicago’s best summer experiences. Because Chicago is so vast and I still have plenty of places I want to try, my list of things to do in Chicago this summer is broken down into two parts – “What I Love” – my own recommendations – and “What I Want to Try” – the places I’ve been dying to go. If you’ve experienced any of the things I want to try, please comment below and let me know how they are!



Al Fresco Dining

outdoor restaurants chicago, chicago summer


\\ What I Love \\

  • The Southern (1840 W. North) – This outdoor, partly-shaded patio gets sweeter every time I go. Refreshing seasonal cocktails are paired with a rotating southern menu, allowing you to try something new each time. When weather permits, the second story opens up with breezy cabanas for hosting your best group of friends. My favorite experiences have included Johnny Cakes, hushpuppies and even an all-you-can-eat crawfish boil.
  • Oak Street Beach Bistro (1001 N. Lake Shore Drive) – While most know about Castaways, Oak Street Beach Bistro is a tamer version at the next beach over. Don’t worry if your feet are covered in sand, stop in for a beer and some fish tacos while you people-watch the afternoon away.
  • Derby (1224 W. Webster) – Also featuring southern fare and drinks, Derby is fun year-round. When it’s a sunny Saturday in the middle of the summer, Derby is my first choice when I’m looking for outside seating – I’ve been lucky enough to get a seat each time! While the brunch menu isn’t that large, their main menu has an extensive list of choices, all of which you can top off with a Mint Julep, Beermosa or Cool as a Cucumber.



\\ What I Want to Try \\

  • RM Champagne Salon (116 N. Green) – Paying homage to one of my favorite drinks, RM Champagne Salon has a courtyard strung with party lights (gorgeous in the pictures). The restaurant opens up at 5 p.m. each night and 11 a.m. on Sundays for brunch. I can see myself lounging under the sparkling lights, ordering a cheese plate while sipping a glass of champagne…
  • Elle on the River (330 N. Wabash) – Situated on the patio outside the Langham Hotel and restaurant Travelle, this sweet new spot is serving up Mediterranean tacos, craft sodas (with the option to add your liquor of choice), and summer-flavored punch bowls titled “Better than a Bradford,” “Elle a Noir” and “Down by the River.” Don’t forget the lovely view of the city over the river.



Rooftop Party Hopping

rooftop bar chicago, chicago summer


\\ What I Love \\

  • ZED451 (739 N. Clark) – While ZED451’s rooftop is only two floors high, it still offers great city views of the surrounding buildings. You’ll enter through the restaurant’s first floor bar, climbing a set of stairs to get to the top. With a number of seating options – long benches, two-seater high-tops and mini cabanas for groups – you can sit down and order a bite off the restaurant’s lighter Cravings menu. This is a great spot for a special event or a night out with friends.
  • J. Parker (1816 N. Clark) – The drinks may be expensive, but the view makes up for it. Take the special elevator up to the top of Hotel Lincoln and step out to incredible visibility of Lincoln Park and the lake. The view encompasses some of Chicago’s best natural beauty and reinforces your love for this great city. Expect a hip see-and-be-seen crowd, and don’t expect to get a seat during peak hours.



\\ What I Want to Try \\

  • I|O Urban Roofscape (127 W. Huron) – Swanky hotel The Godfrey boasts an indoor/outdoor rooftop space serving up food and drinks to its fabulous visitors. Open from breakfast/brunch through late night, the restaurant/bar sits under a retractable roof that allows for year-round entertaining – and they even take reservations! My apartment window overlooks the hotel, leaving me wanting to go every day. One of these days I will make it happen!
  • 52Eighty Rooftop Lounge (166 E. Superior) – Several of my fellow Chicago bloggers made me jealous with their recent pictures from Mile North Hotel’s new rooftop, 52Eighty. Twenty-eight stories up, this brand-new space looks like it’s going to be one of the summer’s hottest rooftops!
  • Little Goat Rooftop (820 W. Randolph) – My Mom and I stumbled across this little gem while waiting to be seated in Little Goat’s main dining room. This cozy space offers cushioned benches, an outdoor bar, and even a few manicured plants and flowers to enhance the atmosphere. Perched on top of the main restaurant, this rooftop offers a great view in the middle of the West Loop. Since it is adjacent to the dining room that can be rented for private events, the rooftop is only open for very specific hours – please check their website for more details.



Fresh Air Fitness

outdoor fitness chicago, outdoor workout chicago, chicago summer


\\ What I Love \\

  • Running the lakefront trail – In my Chicago Marathon training days, I conquered approximately 10 miles (out and back to get in a total of 20!) of that well-worn trail. While the stretch between Fullerton and Oak Street is especially popular due to the beaches, this congested area is not the only scenic part of the route. Heading north between Montrose and Foster you’ll take in expansive fields, nearly empty beaches, and plenty of peaceful spots to camp out for the afternoon. Heading south, you’ll pass by beauties such as the Buckingham Fountain, incredible skyline views by the museum campus, and ultimately more sandy shores looking back up on the loop.
  • The Color Run – Read about my experience at The Color Run and enter to win 2 tickets here.



\\ What I Want to Try \\

  • Yoga at Lincoln Park Zoo’s Nature Boardwalk – Held under the unique wooden sculpture modeled after a turtle shell, weekly yoga classes bring your workouts back to nature. In addition to the picturesque view of the city skyline, you’ll be surrounded by wildlife living in the boardwalk’s ecosystem. Curious? You can even try it out for free – on Saturday, May 31 from 9 – 10 a.m. and Sunday, June 1 from 10 – 11 a.m.
  • Stand-up Paddleboarding – If you haven’t seen pictures of this unique sport, it’s a cross between surfing and kayaking – you’ll stand up on a board and paddle around in the lake. Chicago SUP offers rentals, lessons and even crazy classes such as SUP-Yo (yoga on the board) and SUP-Fit (cross training on the board). Who wants to sign up with me??



Low-Cost Culture & Events

free events chicago, chicago summer


\\ What I Love \\

  • Navy Pier Fireworks – Seeing a spectacle in the sky is not just for 4th of July anymore – in Chicago, you can be dazzled with fireworks every Wednesday at 9:30 p.m. and every Saturday at 10:15 p.m. While you can go directly to Navy Pier to view the fireworks shows, I would recommend finding a rooftop to watch them from, or go out on a fireworks cruise on a boat or kayak.
  • Movies in the Park – Movies in the Park is entering its 14th season, bringing communities together to view classic and modern movies under the stars – for free! Bring your blanket, chairs and picnic to enjoy a balmy evening with friends. I had the pleasure of seeing my favorite movie, Ferris Bueller’s Day Off, at the Chicago History Museum last year. Favorites this summer include:
    • July 5: Gravity at Jonquil Playlot (1001 W. Wrightwood)
    • July 9: Ferris Bueller’s Day Off at Chicago History Museum (1601 N. Clark)
    • July 17: The Sandlot at Wicker Park (1425 N. Damen)
    • August 8: The Goonies at Wrightwood Park (2534 N. Greenview)
    • August 12: The Blind Side at Montgomery Ward Park (630 N. Kingsbury)
    • August 23: Wizard of Oz at Oz Park (2021 N. Burling)
  • Arlington Racetrack – Bring your floppy hats, your sundresses and your bowties to spend a day in the sunshine at Arlington’s beautiful horse racing track. Unlike some of the other horse racing experiences you may have had, you can actually see all of the horses at this track. Even though this location is in the suburbs, it’s easy to take the Metra from Clybourn station and you can even drink on the train. With tickets typically only $12, you’ll get to see the horses race every 20 minutes and grab some food/drinks or place a bet before the next one. The track’s biggest race, the Arlington Million, will be a big party on Saturday, August 16.
  • Farmer’s Markets – There’s nothing like finding fresh inspiration for your dinner from the bountiful produce, meats, cheeses and more flowing from local farmers at Chicago’s many Farmer’s Markets. While my favorite remains the Green City Market in Lincoln Park, many neighborhoods host their own markets on various days of the week, including lunch hours in the Loop. Visit the link above to find one near you.



\\ What I Want to Try \\

  • Jazzin’ at the Shedd – I still haven’t made it to this weekly (every Wednesday 5 – 10 p.m. from June 25 – September 3) summer event, but not for lack of trying! I bought tickets/Groupons the past two years but had conflicts both times. This year I am determined to enjoy the concerts featuring rotating artists outside the Shedd Aquarium. Attendees can choose from various food and beverage options for purchase. Bonus points for fireworks in the background and extended hours on select museum exhibits.
  • Free Concerts at Millennium Park – The gorgeous Jay Pritzker Pavilion hosts free concerts throughout the summer, another great spot to bring a blanket and set up a picnic. There are several sets of concerts – Loops and Variations, which features new music mixed with electronica on Thursdays at 6:30 p.m., and Downtown Sound, which features varied genres of artists every Monday at 6:30 p.m.



Festivals, Concerts and Tours

chicago summer festival, chicago summer concerts, chicago summer


\\ What I Love \\

  • Chicago Pride Parade – This has got to be one of the city’s most fun one-day events. While the Pride Fest takes on a full week of festivities, the parade on June 29 guarantees color, spirit and a whole lot else! Warning: there might be sights you can’t un-see. But don’t let that stop you – the costumes, floats and performances make this a huge street party running for blocks and blocks in Boystown.
  • Chicago Food Planet Tour (Bucktown/Wicker Park) – In addition to getting your fill of Chicago-based delicacies, you’ll be treated to a neighborhood history walking tour. I had the opportunity to learn about the “Beer Baron Mansions,” the painted lady houses, and the history of the park (Wicker Park) itself. This tour also provided my only “official” tutorial on the history, components and principles of the Chicago-style hot dog.
  • Taste of Lincoln Avenue – One of Chicago’s most popular street festivals, Taste of Lincoln Avenue attracts a gathering so large you might end up crowd-surfing. To avoid the congestion, attend at off peak hours, catch one of the local cover bands (such as my favorite 80s cover band, 16 Candles), and sample the flavors of nearby restaurants you’ve never tried. This year’s festival is scheduled for July 26 – 27.



\\ What I Want to Try \\

  • Do-Division Street Fest – Held this upcoming weekend, May 30 – June 1, West Town’s street festival hosts concerts, a sidewalk sale of artisan vendors, local food options and even a fashion festival (runway show!). Centered on the unique businesses and shops that make up the area, this festival gives true neighborhood flair and welcome to visitors from all over.
  • Chicago Blues Fest – I feel like I’ve never fully taken advantage of Chicago’s history of blues music. From June 13 – 15, we can experience numerous blues and honorary acts in Grant Park for free. Headliners include Billy Boy Arnold, Bettye LaVette, Dr. John and more.



Follow The Chicago Lifestyle’s summer adventures around town on Twitter and Instagram.



Which of these have you tried? What tips would you give us for the places we haven’t been? Please comment below!



Chicago Insider Tips: What You Need to Know This Week

The Chicago Lifestyle is bringing you up-to-date Chicago Insider Tips to keep you in the know this week. Free concerts, grill-outs and more – this is where you need to be. Get out and enjoy Chicago (and love the sunshine)!


1. Aloe Blacc Tickets


Take action for a great cause – alleviating poverty – and enter for a chance to win tickets to see Aloe Blacc (the soulful voice behind Avicii’s “Wake Me Up”) at The Vic on April 24. The event is hosted by Global Citizen, who encourages you to take action by learning about the sources of food and water, signing a petition to give children access to education or to help female entrepreneurs rise above poverty. Each action earns you points toward winning a ticket. Sign up here.



2. Big Green Egg Grill-out


Did you attend Better Homes & Gardens/Weber Grill’s Chill and Grill festival in the past? Evidence is sketchy on whether this fun outdoor festival will return to Chicago this year. In the meantime, get your grilling fix this weekend at The Chopping Block Lincoln Square’s event with The Big Green Egg Grill. On the cooking school’s back patio, chefs will be demonstrating the Big Green Egg’s grilling masterpieces with pork and more. Free food for all! No registration necessary, just show up with an appetite! Click here for more details.



3. Chicago Gourmet Tickets


Did you miss Thursday’s discounted pre-sale tickets to Chicago Gourmet? Bummer. This incredible Chicago event isn’t sold out, though. You can still buy full-price tickets on their website. Chicago Gourmet is the foodie fest to end all fests – a full day of wining and dining in Millennium Park’s magnificent space. Chefs from renowned restaurants across the city present their best dishes in sample tents around the park, with a central tent featuring worldly wine vendors. This is an event you do not want to miss – if you can afford a full-price ticket.



4. Title Boxing Club


Title Boxing Club is opening a brand new location in Lincoln Park, at 2417 N. Clark St. Slated to begin their full class schedule the week of May 5, they are offering guests a first class for free! Burn up to 1000 calories an hour in this powerful workout, guaranteed to help you get buff for the summer. Learn more here.